Tracks that are purchased from the iTunes store are often protected with DRM (digital rights management) protection that limits the tracks’ ability to be played, copied, or converted. Such tracks are usually .m4p and sometimes .m4b files.

MediaMonkey for Windows can Sync such files to an iPod, however, for the iPod to be able to play the tracks, the iPod must first be granted rights to the tracks by ‘registering’ with the copy of iTunes that has rights to the tracks. This ‘registration’ can be accomplished as follows:

1. When the iPod is connected to the PC for the first time while iTunes is running, use the ‘Register my iPod’ function from the iPod Setup Assistant).
2. Sync protected content to the iPod using iTunes. This is easiest in most cases:
   1. Run iTunes
   2. Plug in your device (make sure that iTunes is configured to NOT sync automatically)
   3. Right-click on your iPod/iPhone and click ‘Transfer purchases’
   4. Close iTunes

Any iTunes DRMed tracks subsequently Synced with MediaMonkey for Windows should play successfully on the iPod.